(3AS,4R,9BR)-4-(4-HYDROXYPHENYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA[C]CHROMEN-9-OL

Identification

Name
(3AS,4R,9BR)-4-(4-HYDROXYPHENYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA[C]CHROMEN-9-OL
Accession Number
DB08737
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 282.3337
Monoisotopic: 282.125594442
Chemical Formula
C18H18O3
InChI Key
FSYFYSFYUHBIHE-GLJUWKHASA-N
InChI
InChI=1S/C18H18O3/c19-12-9-7-11(8-10-12)18-14-4-1-3-13(14)17-15(20)5-2-6-16(17)21-18/h2,5-10,13-14,18-20H,1,3-4H2/t13-,14+,18+/m1/s1
IUPAC Name
(2R,6S,7R)-7-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁶]trideca-1(13),9,11-trien-13-ol
SMILES
[H][[email protected]@]12CCC[[email protected]]1([H])[[email protected]@]([H])(OC1=CC=CC(O)=C21)C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
16750074
PubChem Substance
99445208
ChemSpider
20581192
BindingDB
19977
HET
WST
PDB Entries
2pog

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0226 mg/mLALOGPS
logP3.77ALOGPS
logP4.11ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity80.5 m3·mol-1ChemAxon
Polarizability30.07 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9943
Blood Brain Barrier+0.8743
Caco-2 permeable+0.6098
P-glycoprotein substrateSubstrate0.5421
P-glycoprotein inhibitor INon-inhibitor0.9602
P-glycoprotein inhibitor IINon-inhibitor0.7878
Renal organic cation transporterNon-inhibitor0.8079
CYP450 2C9 substrateNon-substrate0.7568
CYP450 2D6 substrateNon-substrate0.8654
CYP450 3A4 substrateNon-substrate0.6478
CYP450 1A2 substrateInhibitor0.9371
CYP450 2C9 inhibitorInhibitor0.9048
CYP450 2D6 inhibitorNon-inhibitor0.6896
CYP450 2C19 inhibitorInhibitor0.8962
CYP450 3A4 inhibitorNon-inhibitor0.6566
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7809
Ames testNon AMES toxic0.8104
CarcinogenicityNon-carcinogens0.935
BiodegradationNot ready biodegradable0.9549
Rat acute toxicity2.7283 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8775
hERG inhibition (predictor II)Non-inhibitor0.7453
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 5-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-5 position of the flavonoid skeleton.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Hydroxyflavonoids
Direct Parent
5-hydroxyflavonoids
Alternative Parents
4'-hydroxyflavonoids / Flavans / 1-benzopyrans / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Oxacyclic compounds / Hydrocarbon derivatives
Substituents
4'-hydroxyflavonoid / 5-hydroxyflavonoid / Flavan / 1-benzopyran / Chromane / Benzopyran / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Phenol
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Estrogen receptor alpha
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:34 / Updated on December 01, 2017 16:08